2-[(4-Chlorophenyl)carbonyl]cyclopropanecarbonitrile → 2-[1-(4-Chlorophenyl)-1-hydroxyethyl]cyclopropanecarbonitrile

HRID 561413Notes

Reaction equation

HRID 561413 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:12][CH:11]2[C:13]#[N:14])=[O:9])=[CH:4][CH:3]=1.[CH3:15][Mg]Br>C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:10]2[CH2:12][CH:11]2[C:13]#[N:14])([OH:9])[CH3:15])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 583922662-[(4-Chlorophenyl)carbonyl]cyclopropanecarbonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 583923532-[1-(4-Chlorophenyl)-1-hydroxyethyl]cyclopropanecarbonitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

714 mg of the compound from Example 74A with a purity of 54% (1.89 mmol) were introduced into 7 ml of diethyl ether at RT, 0.94 ml (2.83 mmol) of a 3N solution of methylmagnesium bromide in diethyl ether was added, and the mixture was stirred at RT overnight. The reaction mixture was added to a saturated, ice-cold aqueous ammonium chloride solution, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile-water gradient) to result in 257 mg (55% of theory) of the title compound.

Workup

  1. additionThe reaction mixture was added to a saturated, ice-cold aqueous ammonium chloride solution
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile-water gradient)

Sources & evidence

ORD record
ord-752fafef508b456eb49012ac0ade1d1a
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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